15-hydroxy-9-alpha,13-alpha-epidioxya-abiet-8(14)-en-18-oic acid - Compound Card

15-hydroxy-9-alpha,13-alpha-epidioxya-abiet-8(14)-en-18-oic acid

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15-hydroxy-9-alpha,13-alpha-epidioxya-abiet-8(14)-en-18-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@]1(C)CCC[C@]2(C1CCC1=C[C@@]3(CC[C@]21OO3)C(O)(C)C)C
InChI InChI=1S/C21H32O5/c1-17(2,23)20-11-12-21(26-25-20)14(13-20)7-8-15-18(3,16(22)24-5)9-6-10-19(15,21)4/h13,15,23H,6-12H2,1-5H3/t15?,18-,19+,20+,21-/m1/s1
InChIKey BTNYMWZDBPZWDY-FXYIUBJQSA-N
Formula C21H32O5
HBA 5
HBD 1
MW 364.48
Rotatable Bonds 2
TPSA 64.99
LogP 3.7
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 364.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Juniperus species Cupressaceae Plantae 13100

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2004). Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry,2004,65,2507-2515. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CC(OO2)C=C(C123)CCC4C3CCCC4

Level: 0

Mol. Weight: 364.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.570
Plasma Protein Binding
57.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.360
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.020
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.810
Rat (Acute)
2.510
Rat (Chronic Oral)
1.650
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.980
Hydration Free Energy
-5.110
Log(D) at pH=7.4
3.120
Log(P)
3.75
Log S
-4.65
Log(Vapor Pressure)
-6.05
Melting Point
158.54
pKa Acid
9.93
pKa Basic
5.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8589
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8128
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8126
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7506
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7379
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7325
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7272
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7133
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7014

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